Background: The occurrence of obstetric anal sphincter injuries (OASIS) has increased in most high-income countries during the past twenty years. The consequences of these injuries can be devastating for women and have an impact on their daily life and quality of health. The aim of this study was to obtain a deeper understanding of midwives’ lived experiences of attending a birth in which the woman gets an obstetric anal sphincter injury. Methods: A qualitative study using phenomenological lifeworld research design. The data were collected through in-depth interviews with 13 midwives. Results: The essential meaning of the phenomenon was expressed as a deadlock difficult to resolve between a perceived truth among midwives that a skilled midwife can prevent severe perineal trauma and at the same time a coexisting more complex belief. The more complex belief is that sphincter injuries cannot always be avoided. The midwives tried to cope with their feelings of guilt and wanted to find reasons why the injury occurred. A fear of being exposed and judged by others as severely as they judged themselves hindered the midwives from sharing their experience. Ultimately the midwives accepted that the injury had occurred and moved on without any definite answers. Conclusions: Being caught between an accepted truth and a more complex belief evoked various emotions among the midwives. Feelings of guilt, shame and the midwife’s own suspicion that she is not being professionally competent were not always easy to share. This study shows the importance of creating a safe working environment in which midwives can reflect on and share their experiences to continue to develop professionally. Further research is needed to implement and evaluate the effect of reflective practices in relation to midwifery care and whether this could benefit women in childbirth.